Synthesis of unnatural amino acids functionalized with sterically shielded pyrroline nitroxides

Ying Wang; Joseph T. Paletta; Kathleen Berg; Erin Reinhart; Suchada Rajca; Andrzej Rajca

doi:10.1021/ol502449r

Synthesis of unnatural amino acids functionalized with sterically shielded pyrroline nitroxides

Ying Wang, Joseph T. Paletta, Kathleen Berg, Erin Reinhart, Suchada Rajca, Andrzej Rajca

Chemistry

Research output: Contribution to journal › Article › peer-review

47 Scopus citations

Abstract

A series of unnatural amino acids functionalized with sterically shielded pyrroline nitroxides were synthesized. Their reduction by ascorbate/glutathione indicates that L-cysteine functionalized with gem-diethylpyrroline nitroxide is reduced at the slowest rate and is comparable to that measured for the most resistant to reduction pyrroline and pyrrolidine nitroxides. (Chemical Equation Presented).

Original language	English (US)
Pages (from-to)	5298-5300
Number of pages	3
Journal	Organic Letters
Volume	16
Issue number	20
DOIs	https://doi.org/10.1021/ol502449r
State	Published - Oct 17 2014

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Synthesis of unnatural amino acids functionalized with sterically shielded pyrroline nitroxides",

abstract = "A series of unnatural amino acids functionalized with sterically shielded pyrroline nitroxides were synthesized. Their reduction by ascorbate/glutathione indicates that L-cysteine functionalized with gem-diethylpyrroline nitroxide is reduced at the slowest rate and is comparable to that measured for the most resistant to reduction pyrroline and pyrrolidine nitroxides. (Chemical Equation Presented).",

author = "Ying Wang and Paletta, {Joseph T.} and Kathleen Berg and Erin Reinhart and Suchada Rajca and Andrzej Rajca",

note = "Publisher Copyright: {\textcopyright} 2014 American Chemical Society.",

year = "2014",

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language = "English (US)",

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T1 - Synthesis of unnatural amino acids functionalized with sterically shielded pyrroline nitroxides

AU - Wang, Ying

AU - Paletta, Joseph T.

AU - Berg, Kathleen

AU - Reinhart, Erin

AU - Rajca, Suchada

AU - Rajca, Andrzej

PY - 2014/10/17

Y1 - 2014/10/17

N2 - A series of unnatural amino acids functionalized with sterically shielded pyrroline nitroxides were synthesized. Their reduction by ascorbate/glutathione indicates that L-cysteine functionalized with gem-diethylpyrroline nitroxide is reduced at the slowest rate and is comparable to that measured for the most resistant to reduction pyrroline and pyrrolidine nitroxides. (Chemical Equation Presented).

AB - A series of unnatural amino acids functionalized with sterically shielded pyrroline nitroxides were synthesized. Their reduction by ascorbate/glutathione indicates that L-cysteine functionalized with gem-diethylpyrroline nitroxide is reduced at the slowest rate and is comparable to that measured for the most resistant to reduction pyrroline and pyrrolidine nitroxides. (Chemical Equation Presented).

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ER -

Synthesis of unnatural amino acids functionalized with sterically shielded pyrroline nitroxides

Abstract

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